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Binding of HSO4– vs proton transfer in aminophenyl-substituted adamantane dipyrromethane receptors


Alešković, Marija; Došlić, Nađa; Basarić, Nikola; Mlinarić-Majerski, Kata
Binding of HSO4– vs proton transfer in aminophenyl-substituted adamantane dipyrromethane receptors // 6-ISMSC - International Symposium on Macrocyclic and Supramolecular Chemistry, Brighton, United Kingdom
Brighton, Engleska, 2011. (poster, međunarodna recenzija, sažetak, znanstveni)


Naslov
Binding of HSO4– vs proton transfer in aminophenyl-substituted adamantane dipyrromethane receptors

Autori
Alešković, Marija ; Došlić, Nađa ; Basarić, Nikola ; Mlinarić-Majerski, Kata

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
6-ISMSC - International Symposium on Macrocyclic and Supramolecular Chemistry, Brighton, United Kingdom / - Brighton, Engleska, 2011

Skup
6-ISMSC - International Symposium on Macrocyclic and Supramolecular Chemistry

Mjesto i datum
Brighton, Engleska, 03-07.07.2011

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Proton transfer; pyrrole receptors; UV/Vis and fluorescence spectrometry;

Sažetak
Molecular recognition of anion species by neutral pyrrole receptors is a continuing challenge in the field of anion coordination chemistry.1 We have recently investigated adamantane-dipyrromethanes as potential anion binding agents.2 Our next step was introduction of a chromofore into the binding site, as in I, so that receptors could be employed as chromogenic or fluorogenic sensors. We report the synthesis and anion binding studies of new receptors 1-4 with F–, Cl–, Br–, AcO–, H2PO4–, HSO4–, NO3– in CH3CN by UV/Vis and fluorescence spectrometry. Compared to 1 and 2, receptors 3 and 4, respectively, were expected to form more stable complexes with anions due to the introduction of hydrogen bond donor, amino moiety. However, UV/Vis and fluorescence titrations indicated higher association constants only for HSO4–. That prompted us to investigate whether the obtained values correspond to association constants of the complexes, or proton transfer equilibrium between the HSO4– and NH2 as reported by Bowman-James.3 Therefore we performed a thorough 1H NMR, UV and fluorescence study in the presence of an acid and/or HSO4–. Further, the geometry, energetics and protonation state of the complexes have been investigated at the DFT level using the dispersion-corrected wb97xD functional4 combined with the polarization continuum model.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Kata Majerski, )

Ustanove
Institut "Ruđer Bošković", Zagreb